Diamination/Oxidative Cross-Coupling/Bicyclization of Anilines and Methyl Ketones: Direct I2-Promoted Synthesis of 1,2-Fused Oxindoles
An I 2 -promoted domino bicyclization approach via multiple sequential C–H functionalization was serendipitously discovered for the synthesis of 1,2-fused oxindoles from methyl ketones and anilines. This approach was optimized, resulting in a concise and atom-economical approach for the one-pot construction of 1,2-fused oxindoles from methyl ketones and anilines rather than using preexisting indolin-3-ones or indoles. Mechanistic studies revealed that the key step involved an oxidative cross-coupling between in situ generated phenylglyoxal and α,α-diaminoketone. Graphic Abstract ACS Electronic Supporting Info
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